8 Unspoiled Small Towns in Massachusetts

As the sixth state to join the Union in 1788, Massachusetts is packed with history and culture, and its charming small towns have done a fantastic job of keeping that legacy alive through the ages. From historic reenactment villages to apple orchards and well-preserved lighthouses, there is no shortage of unique, New England attractions to visit. Ready to shake up your vacation routine and explore something fresh? Begin crafting your itinerary for these hidden gem towns!

Concord

History lovers will deeply appreciate the history of Concord, the birthplace of the American Revolution. Today, Concord expresses its history through a number of historical sits, museums, and walking tours. The Concord Museum has a fascinating number of artifacts, including Paul Revere’s 1775 lantern that he placed in Boston’s Old North Church. The Ralph Waldo Emerson House is another historic gem, once home to the famous American poet and philosopher. The Walden Woods Project is the perfect blend of history and nature, preserving land from Henry David Thoreau. In addition to browsing Thoreau-related materials, visitors can stop by the scenic Walden Pond.

Stockbridge

Visitors might be surprised to discover that Stockbridge is home to just 2,000 residents, given its wide variety of summer music festivals, art galleries, museums, theater performances, and beautiful historic homes and gardens. On October 25th, the town will host a Halloween Parade and Party, with a lighted pumpkin walk, Halloween crafts, and a Halloween storytime for the kids. The town decorates its Main Street into a winter wonderland scene in December, especially celebrating the season from December 6th through 8th during its Christmas festival. For those looking for an entertaining show, the Berkshire Theatre Group puts on periodic performances. The Berkshire Botanical Garden is one of the town’s natural highlights, featuring 15 acres of gardens with 25 distinct display areas.

Groton

Groton, Massachusetts, is a laid-back town located in the Nashoba Valley with a population of roughly 11,000 residents. It has an extensive, 130 mile trail network, that allows hikers to explore an impressive variety of landscapes, including glaciers, lakes, rivers, kettle holes, vernal pools, and more. To those familiar with the art world, the small town is also home to two renowned artists: Paul Matisse and Edmund C. Tarbell, whose work can be viewed in town. The town’s culinary scene is also worth highlighting, with standout spots like Filho's Cucina, known for its traditional Italian dishes, and Forge & Vine, a local favorite centered around a massive wood-fire grill—both offering unique dining experiences.

Sandwich

Sandwich has a population of about 20,000 residents and proudly presents itself as the first town settled on Cape Cod. Due to its coastal location, there are plenty of marine-centered outdoor activities to take part in, such as biking along the Cape Cod Canal, the widest canal in the world at sea level. Boating on Cape Cod Bay and kayaking through the town’s salt marshes are two popular activities as well. The town’s historic roots are preserved through the abundance of historic buildings in town, such as the 1834 town hall, in Sandwich’s center, and the Hoxie House, a museum that showcases family life from the 17th century.

Great Barrington

Great Barrington, with a population of just under 7,000, has a long history, with the first European settlers arriving in the late 17th century. Today, the town blends its historic roots with more modern touches, creating a unique mix of charm and contemporary style. It also has its fair share of natural beauty. Monument Mountain is the perfect example, having a 1,642-foot summit with views looking over the Housatonic River Valley. In town, The Mahaiwe Performing Arts Center not only has a beautiful, historic interior, but has an impressive calendar of performances. Cecily Strong, Jane Lynch, and John Mulaney have all performed in the past. Shoppers will have plenty to do in Great Barrington as well, such as visit Rubiner’s Cheesemongers, a famed cheese store, Départ Wine, a wine store, and Familiar Trees, an aesthetic book shop.

Sturbridge

Sturbridge, with a population of roughly 10,000, is perhaps most famously known for being home to Old Sturbridge Village, the largest outdoor museum in New England. The village features over 200 acres and 40 historic buildings, complemented by costumed historians who simulate New England life in the 19th century. There is also a farm on the premises with sheep, cows, pigs, chickens, and more. Brookfield Orchards is another enjoyable attraction, featuring a charming apple orchard and a snack bar including homemade fudge and hot apple dumplings. Hikers can head to the nearby Leadmine Mountain Conservation Area, which has 15 miles of marked trails that pass through pine and oak forests and submerged wetlands.

Newburyport

Located just 35 miles north of Boston, Newburyport is a charming coastal town rich in history and brimming with attractions. History enthusiasts can visit the iconic Plum Island Lighthouse or tour the Spencer-Peirce-Little Farm, which has a long history dating back to the 1690s. The town's lively events calendar is also worth a look, with annual festivities like Oktoberfest, film festivals, art walks, and theater performances. For those who love to shop, Newburyport offers a variety of small businesses, from jewelry and home decor stores to clothing boutiques and wine shops, making it a perfect spot for an afternoon of exploring.

Maynard

Maynard, with a population of about 11,000 residents, has embraced an cultural and vibrant arts scene. ArtSpace Maynard serves as a major hub for the local art scene, offering studio space for artists and showcasing their work in its gallery. The center also hosts a variety of art classes, from block printmaking to seasonal landscape painting. 6 Bridges Gallery, in downtown Maynard, is another great way to experience the town’s art, showcasing a diverse range of artistic styles and media. For those wanting to enjoy the area’s nearby nature, Assabet River Rail Trail is an excellent choice, spanning around 12.5 miles and connecting the towns of Acton, Maynard, Stow, Hudson, and Marlborough.

Final Thoughts

While Boston often attracts tourists to Massachusetts, the true essence of the state’s culture lies in its charming small towns. Don’t let their small populations fool you—these locales boast sophisticated shops, vibrant art galleries, American Revolution museums, and scenic glacier hikes, among other enticing attractions. So, embrace the adventure and think outside the box by adding these eight towns to your itinerary!